Phenyl isocyanate → Methyl 3-benzyl-2-isoxazolin-5-yl(P-methyl)phosphinate

HRID 1084798Notes

Reaction equation

HRID 1084798 reaction equation
C1(N=C=O)C=CC=CC=1.[CH:10]([P:12]([CH3:16])(=[O:15])[O:13][CH3:14])=[CH2:11].C(N(CC)CC)C.[C:24]1([CH2:30][CH2:31][N+:32]([O-])=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[CH2:30]([C:31]1[CH2:11][CH:10]([P:12]([CH3:16])(=[O:15])[O:13][CH3:14])[O:33][N:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 802081-Nitro-2-phenylethaneHCID 6454580Methyl methylvinylphosphinate

Product 1

HCID 20062386Methyl 3-benzyl-2-isoxazolin-5-yl(P-methyl)phosphinateYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Preparation is carried out in analogy to Example 23 from 37.1 ml (0.34 mol) of phenyl isocyanate, 22.5 g (0.187 mol) of methyl vinyl(P-methyl)phosphinate, 4 ml of triethylamine and 25.7 g (0.17 mol) of 2-phenylnitroethane in toluene, resulting in 34 g of brown oil.

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-a078aed30ebf450481812bf743e1fd6f
Source dataset
uspto-grants-1991_04
Patent number
US05006515

Reaction notes

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